Methanol → Ethyl 4-acetyl-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

In a two-neck round bottom flask with an argon inlet, 4.0 g of ethyl pyrrole 2-carboxylate (28.8 mmol) is dissolved in 100 ml of 1,2-dichloroethane. Subsequently, 8.0 g of AlCl3 is added slowly. A solution of 4.4 ml of acetyl chloride (62 mmol) in 50 ml of 1,2-dichloroethane was then added dropwise over a period of 15 min. After stirring the reaction mixture at room temperature for one hour, it is carefully poured onto 200 g of crushed ice. After hydrolysis, the mixture is transferred into a separatory funnel and the organic phase is separated off. The aqueous phase is extracted with dichloromethane (2×200 ml), and the combined organic phases are washed with a saturated solution of aqueous sodium bicarbonate (1×100 ml) and with water (1×100 ml) before being dried over magnesium sulfate. The solvent is then removed under vacuum. Chromatographic workup (silica gel; 1% methanol in dichloromethane as eluent) yielded the product as a pale brown powder (4.0 g, 76% yield). 1H NMR (δ ppm, CDCl3): 10.41 (s, br, 1H, NH); 7.51 (dd, J=3.34, 1.62 Hz, 1H, α-pyrrolic); 7.28 (dd, J=1.62, 2.31 Hz, 1H, β-pyrrolic); 4.29 (q, J=7.12 Hz, 2H, CO2Et); 2.39 (s, 3H, Me); 1.31 (t, J=7.12 H, 3H, CO2Et). 13C NMR (δ ppm, CDCl3): 193.55; 161.07; 127.00; 126.54; 124.04; 114.86; 60.83; 27.13; 14.15. Exact mass calculated for C9H12NO3 (M+H)=182.081718, found=182.081495.

Provenance & Evidence